5-Heptadecyl-1,3-benzenediol

Names

[ Name ]:
5-Heptadecyl-1,3-benzenediol

[Synonym ]:
5-Heptadecyl-1,3-dihydroxybenzene
5-Heptadecyl-1,3-benzenediol
5-N-Heptadecylresorcinol
1,3-DIHYDROXY-5-HEPTADECYLBENZEN
1,3-Benzenediol, 5-heptadecyl-
5-heptadecylbenzene-1,3-diol
5-Heptadecylresorcinol

Biological Activity

[Description]:

5-Heptadecylresorcinol (AR-C17), a phenolic lipid component, is also an orally active mitochondrial protector. 5-Heptadecylresorcinol improves mitochondrial function via sirtuin3 signaling pathway, thus alleviates endothelial cell damage and apoptosis. 5-Heptadecylresorcinol induces sirtuin3-mediated autophagy. 5-Heptadecylresorcinol reduces the atherosclerotic plaques in the aortic root region of mice heart. 5-Heptadecylresorcinol can be used for research of atherosclerosis prevention and obesity[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> Sirtuin

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Cell Cycle/DNA Damage >> Sirtuin

Research Areas >> Metabolic Disease

[Target]

SIRT3

[In Vitro]

5-Heptadecylresorcinol（0、0.5、1 和 2 µM；24 小时）通过上调 HUVEC 中的 SIRT3 减轻线粒体功能障碍[1]。 5-Heptadecylresorcinol 减轻了炎症条件培养基 (CM) 诱导的脂肪细胞脂肪分解和线粒体损伤，同时减弱了线粒体活性氧的产生和线粒体膜去极化[2]。 5-Heptadecylresorcinol（5、10 和 15 μM；24 小时）通过减少 3T3-L1 脂肪细胞中甘油的释放显着防止 CM 诱导的脂肪细胞脂肪分解[2]。 5-Heptadecylresorcinol（5、10 和 15 μM；24 小时）改善 CM 诱导的脂肪细胞线粒体功能障碍[2]。 Western Blot Analysis[2] Cell Line: 3T3-L1 adipocytes Concentration: 5, 10 and 15 μM Incubation Time: 24 hours Result: Increased the expression of UCP1, COX IV, PGC-1α, DRP1 and MFN2 proteins.

[In Vivo]

5-Heptadecylresorcinol（30 mg/kg、150 mg/kg；每日口服，持续 16 周）改善高脂饮食喂养的 ApoE−/− 小鼠的脂质代谢[1]。 5-Heptadecylresorcinol（30 mg/kg、150 mg/kg；每天口服，持续 16 周）增加小鼠体重，减轻脂肪组织巨噬细胞浸润和线粒体功能障碍[2]。 Animal Model: C57BL/6J mice[1][2] Dosage: 30 mg/kg, 150 mg/kg Administration: PO; daily for 16 weeks Result: Lowered serum total cholesterol, triglyceride, VLDL-C, and LDL-C levels[1]. Reduced adipose tissue macrophage infiltration from high-fat diet induced obese C57BL/6J mice[2].

[References]

[1]. Rakshit D, et al. The Pharmacological Activity of Garlic (Allium sativum) in Parkinson's Disease: From Molecular Mechanisms to the Therapeutic Potential. ACS Chem Neurosci. 2023 Mar 15;14(6):1033-1044.

[2]. Yoo DY, et al. Neuroprotective effects of Z-ajoene, an organosulfur compound derived from oil-macerated garlic, in the gerbil hippocampal CA1 region after transient forebrain ischemia. Food Chem Toxicol. 2014 Oct;72:1-7.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
478.0±15.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₄₀O₂

[ Molecular Weight ]:
348.56

[ Flash Point ]:
202.6±15.0 °C

[ Exact Mass ]:
348.302826

[ PSA ]:
40.46000

[ LogP ]:
9.72

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.507

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2907299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2907299090

[ Summary ]:
2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%

Articles

Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis.

Phytochemistry 106 , 156-63, (2014)

Chemical investigation of a sample of propolis originating from North-Western Cameroon led to the isolation of thirteen alk(en)ylphenols (1-13) (inseparable mixture) along with α-amyrin (14), β-amyrin...

5-alk(en)ylresorcinols as the major active components in wheat bran inhibit human colon cancer cell growth.

Bioorg. Med. Chem. 19 , 3973-82, (2011)

We and others have found that wheat bran oil is the active constituent in wheat bran for colon cancer prevention. However, the active components in wheat bran oil are still unknown. Using human colon ...

5-alkylresorcinols from Merulius incarnatus.

J. Nat. Prod. 69 , 704-6, (2006)

Two new, 5-heptadeca-8'Z,11'Z,16-trienylresorcinol (1) and 5-heptadeca-9'E,11'Z,16-trienylresorcinol (2), and six known 5-alkylresorcinols (3-8) were isolated from the mushroom Merulius incarnatus. Co...